Herbicidal composition

ABSTRACT

A herbicidal composition for foliar treatment is described, which contains as active ingredients, (a) a compound of general formula [1] wherein R is alkyl, cycloalkyl, alkenyl, dimethylamino, or diethylamino; and (b) a compound selected from the group consisting of imazethapyr or a salt thereof, imazaquin or a salt thereof, imazamox or a salt thereof, acifluorfen-sodium, lactofen, fomesafen, clethodim, sethoxydim, fenoxaprop-P-ethyl, fluazifop-P-butyl, and quizalofop-P-ethyl. The herbicidal composition is useful for effective control of a wide variety of weeds in upland fields, particularly in soybean fields. Also described are a weeding method by foliar treatment of weeds with the above herbicidal composition; and use as a herbicide for foliar treatment, of a mixture of the above active ingredients. ##STR1##

This Application is a 371 of PCT/JP98/00635 filed Feb. 17, 1998.

TECHNICAL FIELD

The present invention relates to a herbicidal composition, and more particularly, it relates to a herbicidal composition for foliar treatment and a weeding method by foliar treatment of weeds therewith.

BACKGROUND ART

At the present time, numerous herbicides are commercially available and they are widely used. There are, however, many species of weeds to be controlled and their growth extends over a long time. For this reason, requested are herbicides with higher herbicidal activity, wide herbicidal spectrum, and safety to crops.

DISCLOSURE OF INVENTION

The present inventor has intensively studied to find out excellent herbicides. As a result, he has found that various weeds growing in crop lands or non-crop lands can be effectively controlled by foliar treatment of these weeds with a herbicidal composition containing as active ingredients,

(a) a compound of the general formula: ##STR2## wherein R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, C₂ -C₆ alkenyl, dimethylamino, or diethylamino; and

(b) a compound selected from the group consisting of (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid (common name, imazethapyr; hereinafter referred to as imazethapyr) or a salt thereof, (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinoline-carboxylic acid (common name, imazaquin; hereinafter referred to as imazaquin) or a salt thereof, 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(metoxymethyl)-nicotinic acid (common name, imazamox; hereinafter referred to as imazamox) or a salt thereof, sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (common name, acifluorfen-sodium; hereinafter referred to as acifluorfen-sodium), ethyl O-[5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl]-DL-lactate (common name, lacto-fen; hereinafter referred to as lactofen), 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide (common name, fomesafen; hereinafter referred to as fomesafen), (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-[2-(ethyl-thio)propyl]-3-hydroxy-2-cyclohexen-1-one (common name, clethodim; hereinafter referred to as clethodim), 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (common name, sethoxydim; hereinafter referred to as sethoxydim), (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid (common name, fenoxaprop-P-ethyl; hereinafter referred to as fenoxaprop-P-ethyl), butyl (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate (common name, fluazifop-P-butyl; hereinafter referred to as fluazifop-P-butyl), and ethyl (R)-2-[4-(6-chloro-quinoxalin-2-yloxy)phenoxy]propionate (common name, quizalofop-P-ethyl; herein-after referred to as quizalofop-P-ethyl). He has further found that the herbicidal activity is synergistically increased as compared with the cases where the active ingredients are independently used, and the herbicidal composition can, therefore, be applied at a lower amount; and that the herbicidal spectrum is expanded and a wide variety of weeds can be selectively controlled, particularly in soybean fields, thereby completing the present invention.

Thus, the present invention provides a herbicidal composition for foliar treatment comprising as active ingredients, (a) a compound of general formula [1] as depicted above, and (b) a compound selected from the group consisting of imazethapyr or a salt thereof, imazaquin or a salt thereof, imazamox or a salt thereof, acifluorfen-sodium, lactofen, fomesafen, clethodim, sethoxydim, fenoxaprop-P-ethyl, fluazifop-P-butyl, and quizalofop-P-ethyl (hereinafter referred to as the present composition); and a weeding method by foliar treatment of weeds therewith.

In the present composition, the salts mean agrochemically acceptable salts such as alkali metal salts, alkaline earth metal salts, amine salts (e.g., isopropylamine salts), or ammonium salts.

MODE FOR CARRYING OUT THE INVENTION

Compound [1], one of the active ingredients of the present composition, can be produced by the methods as described in the following production examples.

PRODUCTION EXAMPLE 1

To a solution of 5.3 g (53.3 mmol) of sodium acetate mixed with about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoro-acetone, and the mixture was stirred at 70° C. for 20 minutes. The reaction mixture was cooled to room temperature, to which a solution of 5.8 g (21.5 mmol) of 2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the mixture was stirred at room temperature for 1 hour. The ether layer was separated and then concentrated. About 60 ml of tetrahydrofuran (hereinafter referred to as THF) was added to the residue, to which 8.3 g (23.0 mmol) of (carbethoxyethylidene)triphenylphosphorane was added, and the mixture was heated under reflux for 2 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.8 g (10.5 mmol) of 2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethyl-pyridazin-3-one.

Then, 3.5 g (9.7 mmol) of 2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one was dissolved in about 10 ml of concentrated sulfuric acid under ice cooling, and the solution was warmed to room temperature. After ten minutes, about 100 ml of water was added to the reaction mixture. The deposited crystals were collected by filtration, and then washed twice with 20 ml of water and once with 10 ml of hexane in this order. The crystals thus obtained were recrystallized from isopropanol, which afforded 3.2 g (9.9 mmol) of 2-[2-fluoro-4-chloro-5-hydroxy-phenyl]-4-methyl-5-trifluoromethylpyridazin-3-one.

Then, 3.2 g (9.9 mmol) of 2-[2-fluoro-4-chloro-5-hydroxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one was dissolved in about 50 ml of N,N-dimethylform-amide, to which 0.44 g (11 mmol) of sodium hydride (60 wt % oil dispersion) was added at room temperature. The mixture was left stand at room temperature for 30 minutes and then cooled with ice, to which 1.8 g (11 mmol) of ethyl bromoacetate was added. The mixture was stirred at room temperature for 1 hour, to which diethyl ether and water were added in this order to make an extraction. The organic layer was washed with 10% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogen-carbonate solution, and saturated aqueous sodium chloride solution in this order, and then dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 2.4 g (5.5 mmol) of ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoro-methyl-3-pyridazinon-2-yl)phenoxyacetate (compound [1] wherein R is ethyl; herein-after referred to as compound A), m.p., 102.0° C.

PRODUCTION EXAMPLE 2

The same procedure as described in Production Example 1 is repeated, except that the following reaction reagents are substituted for ethyl bromoacetate. Thus, the desired ester derivatives of 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyrida-zinon-2-yl)phenoxyacetic acid can be obtained.

                  TABLE 1                                                          ______________________________________                                                     Ester      Compound  Physical                                        Reaction reagent* produced* symbol property (m.p.)                           ______________________________________                                         Methyl bromoacetate                                                                        Methyl ester                                                                              B         80.4° C.                                 Propyl bromoacetate Propyl ester C 82.9° C.                             Butyl bromoacetate Butyl ester D 75.6° C.                               Pentyl chloroacetate Pentyl ester E                                            Hexyl bromoacetate Hexyl ester F                                               Heptyl bromoacetate Heptyl ester G 63.2° C.                             i-Propyl bromoacetate i-Propyl ester H                                         i-Butyl bromoacetate i-Butyl ester I                                           t-Butyl bromoacetate t-Butyl ester J                                           c-Pentyl bromoacetate c-Pentyl ester K                                         c-Hexyl bromoacetate c-Hexyl ester L                                           Allyl bromoacetate Allyl ester M                                               Vinyl chloroacetate Vinyl ester N                                            ______________________________________                                          *: "i", "t", and "c" mean iso, tertiary, and cyclo, respectively.        

¹ H-NMR (250 MHz or 300 MHz, CDCl₃, TMS, δ (pm))

Compound E

0.88 (3H, t, J=7 Hz), 1.2-1.4 (4H, m), 1.55-1.70 (2H, m), 2.43 (3H, q, J=2 Hz), 4.19 (2H, t, J=7 Hz), 4.68 (2H, s), 6.98 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.99 (1H, s)

Compound H

1.26 (6H, d, J=6.3 Hz), 2.43 (3H, q, J=2 Hz), 4.65 (2H, s), 5.05-5.18 (1H, m), 6.98 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.98 (1H, s)

Compound I

0.90 (6H, d, J=6.6 Hz), 1.85-2.03 (1H, m), 2.42 (3H, q, J=1.8 Hz), 3.98 (2H, d, J=6.5 Hz), 4.70 (2H, s), 6.99 (1H, d, J=6.3 Hz), 7.33 (1H, d, J=9.1 Hz), 7.98 (1H, s)

Compound J

1.45-1.53 (9H, m), 2.39-2.45 (3H, m), 4.58-4.60 (2H, m), 6.96-7.00 (1H, m), 7.30-7.36 (1H, m), 7.96-8.00 (1H, m)

Compound K

1.5-1.9 (8H, m), 2.43 (3H, q, J=2 Hz), 4.65 (2H, s), 5.2-5.4 (1H, m), 6.97 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.98 (1H, s)

Compound M

2.42 (3H, q, J=1.9 Hz), 4.67-4.72 (2H, m), 5.23-5.37 (2H, m), 5.84-5.98 (1H, m), 7.00 (1H, d, J=6.3 Hz), 7.33 (1H, d, J=9.2 Hz), 7.99 (1H, s)

Compound N

2.42 (3H, q, J=1.8 Hz), 4.68-4.71 (1H, m), 4.77 (2H, s), 4.94-5.01 (1H, m), 7.03 (1H, d, J=6.3 Hz), 7.26-7.31 (1H, m), 7.34 (1H, d, J=9.0 Hz), 7.99 (1H, s)

PRODUCTION EXAMPLE 3

First, 1.0 g of the above compound A was dissolved in 15 ml of 1,4-dioxane, to which 15 ml of concentrated hydrochloric acid was added. This solution was warmed to 60° C., stirred for 6 hours, and then extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution in this order, and then dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. The residue was dissolved in 5 g of thionyl chloride, heated under reflux for 1 hour, and then concentrated under reduced pressure. The residue was dissolved in 20 ml of THF at room temperature, to which 0.65 g of N,N-diethylhydroxylamine was added dropwise, and the mixture was then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 1.1 g of O-[2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetyl]-N,N-diethylhydroxyl-amine (compound [1] wherein R is diethylamino; hereinafter referred to as compound O).

¹ H-NMR (250 MHz, CDCl₃, TMS, δ (ppm)) 1.10 (6H, t, J=7.1 Hz), 2.42 (3H, q, J=1.9 Hz), 2.94 (4H, q, J=7.1 Hz), 4.74 (2H, s), 7.01 (1H, d, J=6.3 Hz), 7.33 (1H, d, J=9.1 Hz), 7.97 (1H, s)

PRODUCTION EXAMPLE 4

The same procedure as described in Production Example 3 is repeated, except that N,N-dimethylhydroxylamine is substituted for N,N-diethylhydroxylamine. Thus, O-[2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacet-yl]-N,N-dimethylhydroxylamine (compound [1] wherein R is dimethylamino; herein-after referred to as compound P) can be obtained.

Imazethapyr, imazaquin, acifluorfen-sodium, lactofen, fomesafen, clethodim, sethoxydim, fenoxaprop-P-ethyl, fluazifop-P-butyl, and quizalofop-P-ethyl are compounds as described in Farm Chemicals Handbook, 1995 (published by Meister, Publishing Co., 1995), pages C312, C332, C55, C93, C177, C334, C336, C164, C170, and C318, respectively.

Imazamox is a compound as described in AG CHEM NEW COMPOUND REVIEW, VOLUME 13, 1995 (published by AG CHEM INFORMATION SERVICES, 1995), page 13.

The present invention provides a herbicidal composition that is effective for selective control of a wide variety of weeds and for application to a new cultivation method such as non-tillage cultivation. In particular, the herbicidal composition of the present invention effectively controls the main weeds in soybean fields, e.g., dicotyle-donous plants such as wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), pennsylvania smartweed (Polygonum pensylvanicum), common purslane (Portulaca oleracea), common lambsquarters (Chenopodium album), redroot pigweed (Amaranthus retroflemus), wild mustard (Sinapis arvensis), hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa), ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), common cocklebur (Xanthium strumarium), common sunflower (Helianthus annuus), field bindweed (Convolvulus arvensis), sun spurge (Euphorbia helioscopia), devils beggarticks (Bidens frondosa), and common ragweed (Ambrosia artemisiifolia); and monocotyledonous plants such as barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), yellow foxtail (Setaria glauca), southern crabgrass (Digitaris ciliaris), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), and shattercane (Sorghum bicolor), while it exhibits no significant phytotoxicity on crops such as soybean, and succeeding crops to soybean, such as corn.

In the present composition, the mixing ratio of component (a) to component (b), although it may vary with the species of weeds to be controlled, situation and conditions of application, and other factors, is as follows: The weight ratio of compound [1] to a compound selected from the group consisting of imazethapyr or a salt thereof, imazaquin or a salt thereof, and imazamox or a salt thereof is usually in the range of 1:0.5 to 50. The weight ratio of compound [1] to a compound selected from the group consisting of acifluorfen-sodium, lactofen, fomesafen, clethodim, sethoxydim, fenoxaprop-P-ethyl, fluazifop-P-butyl, and quizalofop-P-ethyl is usually in the range of 1:1 to 100.

The present composition may be usually used in the form of formulations such as emulsifiable concentrates, wettable powders, or flowables, which can be prepared by mixing the composition with solid carriers, liquid carriers, or other bulking agents, and if necessary, adding surfactants or other adjuvants to this mixture. In such a formulation, component (a) and component (b) are usually contained at the total amount of 0.5 to 90 wt %, preferably 1 to 80 wt %.

The solid carrier to be used in the formulation may include, for example, the following materials in fine powder or granule form: clays (e.g., kaolinite, diatomaceous earth, synthetic hydrated silicon oxide, Fubasami clay, bentonite, acid clay); talc and other inorganic minerals (e.g., sericite, powdered quartz, powdered sulfur, activated carbon, calcium carbonate); and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea). The liquid carrier may include, for example, water; alcohols (e.g., methanol, ethanol); ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone); aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, methylnaphthalene); non-aromatic hydrocarbons (e.g., hexane, cyclohexane, kerosine); esters (e.g., ethyl acetate, butyl acetate); nitrites (e.g., acetonitrile, isobutyronitrile); ethers (e.g., dioxane, diisopropyl ether); acid amides (e.g., dimethylformamide, dimethylacetamide); and halogenated hydrocarbons (e.g., dichloroethane, trichloroethylene).

The surfactant may include, for example, alkylsulfate esters; alkylsulfonate salts; alkylarylsulfonate salts; alkyl aryl ethers and their polyoxyethylene derivatives; polyethylene glycol ethers; polyhydric alcohol esters; and sugar alcohol derivatives.

The other adjuvants may include, for example, adhesive agents and dispersing agents, such as casein, gelatin, polysaccharides (e.g., powdered starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, and synthetic watersoluble polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid); and stabilizers such as PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methyl-phenol), BHA (2-/3-tert-butyl-4-methyoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.

The present composition can also be prepared by making the active ingredients into the respective formulations using the above formulation technique and then mixing these formulations.

The present composition thus formulated may be applied to plants as such, or after diluted with water or other solvents. The present composition may also be used in admixture with other herbicides, in which case the herbicidal activity can be expected to be enhanced. The present composition can also be used together with insecticides, bactericides, fungicides, plant growth regulators, fertilizers, soil conditioners, or other agents.

The application amount of the present composition, although it may vary with the mixing ratio of component (a) to component (b) as the active ingredient compounds, weather conditions, formulation types, application times, application methods, application places, weeds to be controlled, and crops to be protected, is usually in the range of 5 to 500 g as the total amount of active ingredient compounds per hectare for a mixture of compound [1] and imazethapyr, a salt thereof, imazaquin, a salt thereof, imazamox, or a salt thereof; 10 to 2000 g, preferably 10 to 200 g, as the total amount of active ingredient compounds per hectare for a mixture of compound [1] and acifluorfen-sodium, lactofen, or fomesafen; and 10 to 2000 g as the total amount of active ingredient compounds per hectare for a mixture of compound [1] and clethodim, sethoxydim, fenoxaprop-P-ethyl, fluazifop-P-butyl, and quizalofop-P-ethyl. In the case of emulsifiable concentrates, wettable powders, flowables, or other similar formulations, they are usually applied after diluted in their prescribed amounts with water at a ratio of 100 to 1000 liters per hectare.

The following will describe formulation examples, in which parts are by weight.

FORMULATION EXAMPLE 1

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 35 parts of imazethapyr, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 50 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 2

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 35 parts of imazaquin, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 50 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 3

Twenty parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 40 parts of imazamox, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 35 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 4

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 20 parts of imazamox, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 70 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 5

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 35 parts of imazethapyr, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 49 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 6

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 35 parts of imazaquin, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 49 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 7

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 20 parts of imazamox, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 8

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 10 parts of imazamox, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 79 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 9

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 50 parts of lactofen, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 35 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 10

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 70 parts of acifluorfen-sodium, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 20 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 11

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 70 parts of fomesafen, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 20 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 12

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 25 parts of lactofen, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 13

Two parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 30 parts of acifluorfen-sodium, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 62 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 14

Two parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 30 parts of fomesafen, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 15

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 50 parts of clethodim, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 35 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 16

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 25 parts of crethodim, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 65 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 17

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 50 parts of sethoxydim, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 35 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 18

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 25 parts of crethodim, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 19

Two and a half parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 12.5 parts of clethodim, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 79 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 20

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 25 parts of sethoxydim, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 21

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 35 parts of fenoxaprop-P-ethyl, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 50 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 22

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 50 parts of quizalofop-P-ethyl, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 40 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 23

Ten parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 50 parts of fluazifop-P-butyl, 3 parts of calcium lignin sulfonate, 2 parts of sodium laurylsulfate, and 35 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 24

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 17.5 parts of fenoxaprop-P-ethyl, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 71.5 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 25

Two parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 20 parts of quizalofop-P-ethyl, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 72 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

FORMULATION EXAMPLE 26

Five parts of compound A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, or P, 25 parts of fluazifop-P-butyl, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose), and 64 parts of water are mixed and wet pulverized until the particle size comes to 5 microns or smaller to give a flowable for each compound.

The following will describe test examples.

Evaluation Criteria

The herbicidal activity is evaluated at 11 levels with indices of 0 to 10, i.e., shown by numeral "0", "1", "2", "3", "4", "5", "6", "7", "8", "9", or "10", wherein "0" means that there was no or little difference in the degree of germination or growth between the treated plants and the untreated plants at the time of examination, and "10" means that the test plants died completely or their germination or growth was completely inhibited. The herbicidal activity is excellent when ranked at "7", "8", "9", or "10", but insufficient when ranked at "6" or lower. The phytotoxicity is shown by "no injury" when no significant phytotoxicity was observed; "low" when low phytotoxicity was observed; "moderate" when moderate phytotoxicity was observed; or "high" when high phytotoxicity was observed.

TEST EXAMPLE 1

Plastic pots each having an area of 26.5×19 cm² and a depth of 7 cm were filled with upland soil, and then seeded with soybean (Glycine max), giant foxtail (Setaria faberi), and southern crabgrass (Digitaria ciliaris). These test plants were grown in a greenhouse for 23 days.

An emulsifiable concentrate of compound E, which had been obtained by well mixing 10 parts of compound E, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, a formulation product of imazethapyr (trade name, Pursuit; American Cyanamid Co.), and a mixture of the emulsifiable concentrate of compound E and the formulation product of imazethapyr were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants with a small sprayer. The same procedure was repeated for compound O. After the application, the test plants were grown in the greenhouse for 4 days, and the herbicidal activity and safety to soybean were then examined. The results are shown in Table 2.

                  TABLE 2                                                          ______________________________________                                                      Herbicidal activity                                                         Dosage   southern          Phytotoxicity                               Compound (g/ha) crabgrass giant foxtail soybean                              ______________________________________                                         Compound E                                                                               20       3         4       no injury                                   Compound O 20 3 4 no injury                                                    Imazethapyr 40 4 2 no injury                                                   Compound E +  20 + 40 9 8 no injury                                            imazethapyr                                                                    Compound O + 20 + 40 9 8 no injury                                             imazethapyr                                                                  ______________________________________                                    

TEST EXAMPLE 2

A upland field was seeded with soybean (Glycine max), and the plant was grown for 19 days.

A flowable of compound A, which had been obtained by mixing 10 parts of compound A, 2 parts of a mixture of polyoxyethylene alkylarylphosphate and polyoxyethylene alkyl aryl ether, and 25 parts of water, pulverizing the mixture by wet grinding method so that the particle size came to 5 microns or smaller, adding 11 parts of a thickening agent (xanthan gum and smectite clay) and an antifreezing agent (propylene glycol) to the pulverized mixture, and further adding water so that the total amount came to 100 parts, a formulation product of imazethapyr as described above, and a mixture of the flowable of compound A and the formulation product of imazethapyr were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants, i.e., soybean (Glycine max) and pennsylvania smartweed (Polygonum pensylvanicum) growing in the field, with a sprayer installed on a tractor. On the 7th day after the application, the herbicidal activity and safety to soybean were then examined. The results are shown in Table 3.

                  TABLE 3                                                          ______________________________________                                                             Herbicidal                                                     activity                                                                      Dosage pennsylvania Phytotoxicity                                             Compound (g/ha) smartweed soybean                                            ______________________________________                                         Compound A  20      5            no injury                                       Imazethapyr 70 3 no injury                                                     Compound A + 20 + 70 10 no injury                                              imazethapyr                                                                  ______________________________________                                    

TEST EXAMPLE 3

Plastic pots each having an area of 26.5×19 cm² and a depth of 7 cm were filled with upland soil, and then seeded with soybean (Glycine max), giant foxtail (Setaria faberi), and southern crabgrass (Digitaria ciliaris). These test plants was grown in a greenhouse for 23 days.

An emulsifiable concentrate of compound A, which had been obtained by well mixing 10 parts of compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, a formulation product of lactofen (trade name, Cobra; Valent U.S.A. Co.), and a mixture of the emulsifiable concentrate of compound A and the formulation product of lactofen were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants with a small sprayer. The same procedure was repeated for compounds E and O. After the application, the test plants were grown in the greenhouse for 4 days, and the herbicidal activity and safety to soybean were then examined. The results are shown in Table 4.

                  TABLE 4                                                          ______________________________________                                                      Herbicidal activity                                                         Dosage   southern          Phytotoxicity                               Compound (g/ha) crabgrass giant foxtail soybean                              ______________________________________                                         Compound A                                                                               20       3         4       no injury                                   Compound E 20 3 4 no injury                                                    Compound O 20 3 4 no injury                                                    Lactofen 60 5 4 no injury                                                      Compound A +  20 + 60 10 10 no injury                                          lactofen                                                                       Compound E + 20 + 60 10 10 no injury                                           lactofen                                                                       Compound O + 20 + 60 10 10 no injury                                           lactofen                                                                     ______________________________________                                    

TEST EXAMPLE 4

Plastic pots each having an area of 26.5×19 cm² and a depth of 7 cm were filled with upland soil, and then seeded with soybean (Glycine max), giant foxtail (Setaria faberi), and southern crabgrass (Digitaria ciliaris). These test plants was grown in a greenhouse for 23 days.

An emulsifiable concentrate of compound A, which had been obtained by well mixing 10 parts of compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, a formulation product of clethodim (trade name, Select; Valent U.S.A. Co.), and a mixture of the emulsifiable concentrate of compound A and the formulation product of clethodim were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants with a small sprayer. The same procedure was repeated for compounds E and O. After the application, the test plants were grown in the greenhouse for 4 days, and the herbicidal activity and safety to soybean were then examined. The results are shown in Table 5.

                  TABLE 5                                                          ______________________________________                                                      Herbicidal activity                                                         Dosage   southern          Phytotoxicity                               Compound (g/ha) crabgrass giant foxtail soybean                              ______________________________________                                         Compound A                                                                               20       3         4       no injury                                   Compound E 20 3 4 no injury                                                    Compound O 20 3 4 no injury                                                    Clethodim 20 2 2 no injury                                                     Compound A +  20 + 20 9 9 no injury                                            clethodim                                                                      Compound E + 20 + 20 9 9 no injury                                             clethodim                                                                      Compound O + 20 + 20 9 9 no injury                                             clethodim                                                                    ______________________________________                                    

TEST EXAMPLE 5

Plastic pots each having an area of 26.5×19 cm² and a depth of 7 cm were filled with upland soil, and then seeded with soybean (Glycine max), giant foxtail (Setaria faberi), and southern crabgrass (Digitaria ciliaris). These test plants was grown in a greenhouse for 23 days.

An emulsifiable concentrate of compound A, which had been obtained by well mixing 10 parts of compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, a formulation product of fenoxaprop-P-ethyl (trade name, Pumas; Hoechst A.G.), and a mixture of the emulsifiable concentrate of compound A and the formulation product of fenoxaprop-P-ethyl were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants with a small sprayer. The same procedure was repeated for compounds E and O. After the application, the test plants were grown in the greenhouse for 4 days, and the herbicidal activity and safety to soybean were then examined. The results are shown in Table 6.

                  TABLE 6                                                          ______________________________________                                                      Herbicidal activity                                                         Dosage   southern          Phytotoxicity                               Compound (g/ha) crabgrass giant foxtail soybean                              ______________________________________                                         Compound A                                                                               20       3         4       no injury                                   Compound E 20 3 4 no injury                                                    Compound O 20 3 4 no injury                                                    Fenoxaprop-P- 20 2 2 no injury                                                 ethyl                                                                          Compound A +  20 + 20 9 9 no injury                                            fenoxaprop-P-                                                                  ethyl                                                                          Compound E + 20 + 20 9 9 no injury                                             fenoxaprop-P-                                                                  ethyl                                                                          Compound O + 20 + 20 9 9 no injury                                             fenoxaprop-P-                                                                  ethyl                                                                        ______________________________________                                    

TEST EXAMPLE 6

Plastic pots each having an area of 26.5×19 cm² and a depth of 7 cm were filled with upland soil, and then seeded with soybean (Glycine max), giant foxtail (Setaria faberi), southern crabgrass (Digitaria ciliaris), and barnyardgrass (Echinochloa crus-galli). These test plants were grown in a greenhouse for 23 days.

An emulsifiable concentrate of compound A, which had been obtained by well mixing 10 parts of compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, a formulation product of imazaquin (trade name, Scepter; American Cyanamid Co.), acifluorfen-sodium (trade name, Blazer; BASF A.G.), fomesafen (trade name, Reflex; Zeneca Ag Products), sethoxydim (trade name, Poast; BASF A.G.), fluazifop-P-butyl (trade name, Fusilade; Zeneca Ag Products), quizalofop-P-ethyl (trade name, AssureII; Du Pont Co.), a mixture of the emulsifiable concentrate of compound A and the formulation product of imazaquin, a mixture of the emulsifiable concentrate of compound A and the formulation product of acifluorfen-sodium, a mixture of the emulsifiable concentrate of compound A and the formulation product of fomesafen, a mixture of the emulsifiable concentrate of compound A and the formulation product of sethoxydim, a mixture of the emulsifiable concentrate of compound A and the formulation product of fluazifop-P-butyl, and a mixture of the emulsifiable concentrate of compound A and the formulation product of quizalofop-P-ethyl were independently diluted in their prescribed amounts with water. Each dilution was uniformly sprayed over the test plants with a small sprayer. After the application, the test plants were grown in the greenhouse for 5 days, and the herbicidal activity and safety to soybean were then examined. The results are shown in Table 7.

                  TABLE 7                                                          ______________________________________                                                     Herbicidal activity                                                                            Phyto-                                                      Dosage   giant   southern                                                                              barn-  toxicity                                 Compound (g/ha) foxtail crabgrass yardgrass soybean                          ______________________________________                                         Compound A                                                                               20      4       4      6      no injury                                Imazaquin  35 2 1 1 no injury                                                  Acifluorfen- 180 3 3 2 no injury                                               sodium                                                                         Fomesafen 210 3 3 2 no injury                                                  Sethoxydim 100 2 2 2 no injury                                                 Fluazifop-P- 100 2 2 2 no injury                                               butyl                                                                          Quizalofop-P- 100 2 2 2 no injury                                              ethyl                                                                          Compound A + 20 + 35  8 8 8 no injury                                          imazaquin                                                                      Compound A + 20 + 180 9 9 9 no injury                                          acifluorfen-                                                                   sodium                                                                         Compound A + 20 + 210 9 9 9 no injury                                          fomesafen                                                                      Compound A + 20 + 100 8 8 9 no injury                                          sethoxydim                                                                     Compound A + 20 + 100 9 9 9 no injury                                          fluazifop-P-                                                                   butyl                                                                          Compound A + 20 + 100 9 9 9 no injury                                          quizalofop-P-                                                                  ethyl                                                                        ______________________________________                                    

Industrial Applicability

A wide variety of weeds in upland fields, particularly in soybean fields, can be effectively controlled by the present composition. 

What is claimed is:
 1. A herbicidal composition for foliar treatment comprising as active ingredients,(a) a compound of the general formula: ##STR3## wherein R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, C₂ -C₆ alkenyl, dimethylamino, or diethylamino; and (b) a compound selected from the group consisting of (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid (imazethapyr) or a salt thereof, (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid (imazaquin) or a salt thereof, 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(methoxymethyl)nicotinic acid (imazamox) or a salt thereof, sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (acifluorfen-sodium), ethyl O-[5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl]-DL-lactate (lactofen), 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide (fomesafen), (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (clethodim), 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (sethoxydim), (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid (fenoxaprop-P-ethyl), butyl (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate (fluazifop-P-butyl), and ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate (quizalofop-P-ethyl).
 2. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is imazethapyr, a salt thereof, imazaquin, a salt thereof, imazamox, or a salt thereof.
 3. The herbicidal composition for foliar treatment according to claim 2, wherein the weight ratio of component (a) to component (b) is 1:0.5 to
 50. 4. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is imazethapyr, a salt thereof, imazaquin, a salt thereof, imazamox, or a salt thereof.
 5. The herbicidal composition for foliar treatment according to claim 4, wherein the weight ratio of component (a) to component (b) is 1:0.5 to
 50. 6. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is acifluorfen-sodium, lactofen, or fomesafen.
 7. The herbicidal composition for foliar treatment according to claim 6, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 8. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is acifluorfen-sodium, lactofen, or fomesafen.
 9. The herbicidal composition for foliar treatment according to claim 8, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 10. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is clethodim or sethoxydim.
 11. The herbicidal composition for foliar treatment according to claim 10, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 12. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is clethodim or sethoxydim.
 13. The herbicidal composition for foliar treatment according to claim 12, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 14. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is fenoxaprop-P-ethyl, fluazifop-P-butyl, or quizalofop-P-ethyl.
 15. The herbicidal composition for foliar treatment according to claim 14, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 16. The herbicidal composition for foliar treatment according to claim 1, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is fenoxaprop-P-ethyl, fluazifop-P-butyl, or quizalofop-P-ethyl.
 17. The herbicidal composition for foliar treatment according to claim 16, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 18. A weeding method comprising foliar treatment of weeds with an effective amount of a herbicidal composition containing as active ingredients,(a) a compound of the general formula: ##STR4## wherein R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, C₂ -C₆ alkenyl, dimethylamino, or diethylamino; and (b) a compound selected from the group consisting of (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid (imazethapyr) or a salt thereof, (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid (imazaquin) or a salt thereof, 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(methoxymethyl)nicotinic acid (imazamox) or a salt thereof, sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (acifluorfen-sodium), ethyl O-[5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoyl]-DL-lactate (lactofen), 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide (fomesafen), (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (clethodim), 2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (sethoxydim), (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid (fenoxaprop-P-ethyl), butyl (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate (fluazifop-P-butyl), and ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate (quizalofop-P-ethyl).
 19. The weeding method according to claim 18, wherein the herbicidal composition is applied to the weeds in soybean fields.
 20. The weeding method according to claim 18, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is imazethapyr, a salt thereof, imazaquin, a salt thereof, imazamox, or a salt thereof.
 21. The weeding method according to claim 20, wherein the weight ratio of component (a) to component (b) is 1:0.5 to
 50. 22. The weeding method according to claim 20 or 21, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 5 to 500 g/ha.
 23. The weeding method according to claim 20, 21, or 22, wherein the herbicidal composition is applied to the weeds in soybean fields.
 24. The weeding method according to claim 18, whereincomponent (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is imazethapyr, a salt thereof, imazaquin, a salt thereof, imazamox, or a salt thereof.
 25. The weeding method according to claim 24, wherein the weight ratio of component (a) to component (b) is 1:0.5 to
 50. 26. The weeding method according to claim 24 or 25, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 5 to 500 g/ha.
 27. The weeding method according to claim 24, 25, or 26 wherein the herbicidal composition is applied to the weeds in soybean fields.
 28. The weeding method according to claim 18, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is acifluorfen-sodium, lactofen, or fomesafen.
 29. The weeding method according to claim 28, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 30. The weeding method according to claim 28 or 29, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 200 g/ha.
 31. The weeding method according to claim 28, 29, or 30, wherein the herbicidal composition is applied to the weeds in soybean fields.
 32. The weeding method according to claim 28, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is acifluorfen-sodium, lactofen, or fomesafen.
 33. The weeding method according to claim 32, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 34. The weeding method according to claim 32 or 33, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 200 g/ha.
 35. The weeding method according to claim 32, 33, or 34, wherein the herbicidal composition is applied to the weeds in soybean fields.
 36. The weeding method according to claim 28, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is clethodim or sethoxydim.
 37. The weeding method according to claim 36, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 38. The weeding method according to claim 36 or 37, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 2000 g/ha.
 39. The weeding method according to claim 36, 37, or 38, wherein the herbicidal composition is applied to the weeds in soybean fields.
 40. The weeding method according to claim 18, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is clethodim or sethoxydim.
 41. The weeding method according to claim 40, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 42. The weeding method according to claim 40 or 41, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 2000 g/ha.
 43. The weeding method according to claim 40, 41, or 42, wherein the herbicidal composition is applied to the weeds in soybean fields.
 44. The weeding method according to claim 18, wherein component (a) is compound [1] in which R is C₁ -C₇ alkyl, C₅ -C₆ cycloalkyl, or C₂ -C₆ alkenyl, and component (b) is fenoxaprop-P-ethyl, fluazifop-P-butyl, or quizalofop-P-ethyl.
 45. The weeding method according to claim 44, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 46. The weeding method according to claim 44 or 45, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 2000 g/ha.
 47. The weeding method according to claim 44, 45, or 46, wherein the herbicidal composition is applied to the weeds in soybean fields.
 48. The weeding method according to claim 18, wherein component (a) is compound [1] in which R is dimethylamino or diethylamino, and component (b) is fenoxaprop-P-ethyl, fluazifop-P-butyl, or quizalofop-P-ethyl.
 49. The weeding method according to claim 48, wherein the weight ratio of component (a) to component (b) is 1:1 to
 100. 50. The weeding method according to claim 48 or 49, wherein the herbicidal composition is applied to the weeds so that the total amount of component (a) and component (b) is 10 to 2000 g/ha.
 51. The weeding method according to claim 48, 49, or 50, wherein the herbicidal composition is applied to the weeds in soybean fields. 